Water → HCID 54087283, compound

HRID 981012Notes

Reaction equation

HRID 981012 reaction equation
[CH:1]1([OH:14])[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]1[OH:13].[CH3:15][CH2:16][CH2:17][CH2:18][CH:19]=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Cl-].[Na+].O>[CH2:16]([CH:15]1[O:13][CH:2]2[CH:1]([CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]2)[O:14]1)[CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 8063PentanalHCID 107382HCID 107382, compound

Product 1

HCID 54087283HCID 54087283, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

5 g of 5,9-cyclododecadien-1,2-diol, 2.4 g of valeric aldehyde, a spatula of p-toluenesulfonic acid and 200 ml of 80/100 petroleum ether were charged into a 250 ml two-neck flask equipped with a water separator and the mixture was taken to reflux for 1 h. The reaction mixture was then poured on ice, neutralized with brine, dried and concentrated. Distillation in a bulb-to-bulb apparatus produced 6.06 g of 14-butyl-13,15-dioxabicyclo[10.3.0]pentadeca-4,8-diene.

Workup

  1. temperatureto reflux for 1 h
  2. additionThe reaction mixture was then poured on ice
  3. customdried
  4. concentrationconcentrated
  5. distillationDistillation in a bulb-to-bulb apparatus

Sources & evidence

ORD record
ord-7ed73a277c27453eb32791a42960d9ec
Source dataset
uspto-grants-1991_02
Patent number
US04990495

Reaction notes

Loading…